Substituted ureas



2,870,205 7 SUBSTITUTED UREAS David J. Beaver, Richmond Heights, andPaul I. Stotfel,

St. Louis, Mo., assignors to Monsanto Chemical Company, St. Louis, Mo.,a corporation of Delaware Application October 18, 1956 Serial No.616,592

6 Claims. (Cl. 260-553) No Drawing.

This invention relates to new and useful substituted ureas and toprocesses for making same.

The substituted ureas of this invention may be represented by thestructure .1-(3,4dichlorophenyl) 3-(3-hydroxypropyl) urea1-(3,4-dibromophenyl) 3-(3-hydroxypropyl) urea 1-(3,5-dichlorophenyl)3-(3-hydroxypropyl) urea 1-(3,5-dibromophenyl) 3-(3-hydroxypropyl) urea1-(3,4,5-trichlorophenyl) 3-(3-hydroxypropyl) ureal-(3,4,5-tribromophenyl) 3-(3-hydroxypropyl) 'urea As illustrative ofthe preparation of the compounds of this invention is the following:

Example I To a suitable reaction vessel equipped with an agitator isadded and mixed approximately 18.8 parts by weight of3,4-dichlorophenylisocyanate, approximately 7.5 parts by weight of3-amino-1-propanol and approximately 54 parts by weight of diethylether. The reaction is exothermic and upon its completion, as evidencedby a temperature drop, the mass is cooled and permitted to stand for onehour at room temperature. The mass is filtered and the filter cake iswashed with two successive 18 parts by weight portions of diethyl ether.Upon air drying the filter cake, approximately 26 parts by weight of l-(3,4-dichlorophenyl) 3-(3-hydroxypropyl) urea is obtained as whitegranules, M. P. 126.5- 128 C.

Example II Employing the procedure of Example I but replacing3,4-dichlorophenylisocyanate with an equal weight of3,5-dichlorophenylisocyanate, there is obtained 1-(3,5- dichlorophenyl)3-(3-hydroxypropyl) urea.

Example Ill Employing the procedure of Example I but replacing3,4-dichlorophenylisocyanate with a' chemically equivalent weight of3,4,5-trichlorophenylisocyanate, there is obtained1-(3,4,5-trichlorophenyl) 3-(3-hydroxypropyl) urea.

Example IV Employing the procedure of Example I but replacing3,4-dichlorophenylisocyanate with a chemically equivalent weight of3,4-dibromophenylisocyanate, there is obtained 1-(3,4-dibromophenyl)3'(3-hydroxyproPYl) urea.

In the preparation of the new compounds of this invention other inertsolvents than diethyl ether may be employed, e. g. di-isopropyl ether,methyl butyl ether,

United States Patent Patented Jan. 2 1959 ICE ' 2 the liquid alkanes,and the like. The reaction tempera ture employed in making the newcompounds may vary widely but ingcneral will be .between roomtemperature and the reflux temperature of the system.

The compounds of this invention are particularly useful in controllingbacterial growth, especially M icrococcus pyogenes var. aureus. In thisregard the substituted ureas of this invention when compounded with adetergent soap (i. e. an alkali metal salt of a fatty acid of animal orvegetableorigin such as stearic acid, lauric acid, palmitic acid, ole'iccid, ricinoleic acid, myristic acid, and the like,

or mixtures thereof obtained from tallow, lard, coconut Percent Oleicand linoleic acid About 46 Stearic About 14 Palmitic acid -l. About 30Lower fatty acids, e. g. myristic, lauric, etc About 10) and compared tol-(3,4-dichlorophenyl) 3-(2-hydroxypropyl) urea (a white solid meltingat 152.0152.8 C.

prepared from 3,4-dichlorophenylisocyanate and 2-hydroxy-n-propylaminein accordance with the process of Example I). The respective compoundswere incorporated in the said alkali metal fatty acid soap in a weightratio of 1 part to 50 parts soap. Aliquots of each were added to aSabourards dextrose agar medium so as to give concentrations of 1, 10and parts per 100,000 of the respective urea derivatives in the agar.The agar in each case was then poured into a petri dish, allowed toharden, and then inoculated with a standard culture of Micrococcuspyogenes var. aureus of standard resistance. The incubation in eachinstance was made at 37 C. for 48 hours. The extent of growth is notedbelow:

Compound/Concentration in parts per 100,00(

1-(3,4-dich1oropheny1) 3-(2-hydroxypropyl) urea. 1-(3.4-rlichl0rophenyl)3-(3-hydroxypropyl) urea.

none. heavy. heavy.

droxypropyl) urea with an equal weight of 1-(3,5-dichlorophenyl)3-(3-hydroxypropyl) urea or 1-(3,4,5-trichlorophenyl)3-(3-hydroxypropyl) urea. Similar control is obtained employing thecorresponding bromine substituted analogues thereof.

Relatively small amounts of these new substituted ureas in a detergentsoap composition have been found to yield efiective antiseptic detergentsoap compositions. Amounts as low as 0.5% by weight based on the weightof the detergent soap have proved satisfactory. However, it is preferredto employ amounts in the order of l to 5% by weight. Larger amounts, e.g. up to 10% by weight, may be employed, however, such upper limit willbe determined by practical considerations.

While this invention has been described with respect to certainembodiments, it is not so limited and it is to be understood thatvariations and modifications thereof What is claimed is: l 6. Theprocess of making the compounds of claim 1, 1. Compounds of thestructure which comprises reacting in substantially equimolecularproportions 3-amino-l-propanol and an isocyanate of the 5 ing the samesignificance as in claim 1, in the presence of an inert solvent at atemperature in the range of room where X C is a halo en substituted: henl: radical n 6H5 g p y temperature to the reflux temperature of thesystem.

free of substituents ortho to the nitrogen atom,- where X gf ii ig fgand where n 18 a whole number r References Cited in the file of thispatent 2. Compounds of claim 1 where X is selected from 10 UNITED STATESPATENTS the g p consisting of bromine n chlorine 3,663,729 m et a1D6012, 1953 wgrgrclarrrlugggnds of claim 1 wherein X 18 chlorine andOTHER REFERENCES 4. 1-(3,4-dichlorophenyl) 3-(3-hydroxypropyl) urea.Thompson et al.: Botanical Gazette, vol. 107: pages 5.1-(3,5-dichlorophenyl) 3-(3-hydroxypropyl) urea. 15 494 to 498 (1946).

1. COMPOUNDS OF THE STRUCTURE